199327-63-4

Basic information

• Product Name: 6-CYANOOXINDOLE
• Synonyms: 2-Oxo-2,3-dihydro-1H-indole-6-carbonitrile;2-Oxo-2H-indole-6-carbonitrile;6-CYANOOXINDOLE;6-Cyanoindole-2-one;2-oxoindoline-6-carbonitrile;2-oxo-2,3,3a,7a-tetrahydro-1H-indole-6-carbonitrile;6-Cyano-2-oxoindole;REF DUPL: 6-Cyano-2-oxoindole
• CAS NO: 199327-63-4
• Molecular Formula: C₉H₆N₂O
• Molecular Weight: 158.16
• Product Categories: blocks;Carboxes;IndolesOxindoles;Indoline & Oxindole
• Mol File: 199327-63-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 369.4 °C at 760 mmHg
• Flash Point: 177.2 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 1.19E-05mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6-CYANOOXINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CYANOOXINDOLE(199327-63-4)
• EPA Substance Registry System: 6-CYANOOXINDOLE(199327-63-4)

Safety Data

• Hazardous Substances Data: 199327-63-4(Hazardous Substances Data)

Usage

General Description

6-Cyanooxindole is a chemical compound with the molecular formula C9H5NO. It is a heterocyclic compound that contains both a cyanide group and an oxindole moiety. 6-Cyanooxindole is commonly used as a building block in organic synthesis, particularly in the preparation of pharmaceuticals and agrochemicals. It serves as a versatile precursor in the construction of various chemical structures due to its reactivity and potential for functional group transformations. Additionally, 6-Cyanooxindole has been studied for its potential biological activities, including antiproliferative and anticancer properties. Overall, 6-Cyanooxindole is a valuable and versatile chemical that has applications in both the laboratory and in various industries.

InChI:InChI=1/C9H6N2O/c10-5-6-1-2-7-4-9(12)11-8(7)3-6/h1-3H,4H2,(H,11,12)

Upstream product

• 651747-69-2 2-(4-cyano-2-nitrophenyl)malonic acid dimethyl ester 
• 939-80-0 4-chloro-3-nitrobenzonitrile 
• 652997-62-1 methyl 2-(2-amino-4-cyanophenyl)acetate 
• 557-21-1 zinc(II) cyanide 
• 99365-40-9 6-bromo-2,3-dihydro-1H-indole-2-one 
• 651747-70-5 2-(4-cyano-2-nitrophenyl)acetic acid methyl ester 
• 557-21-1 dicyanozinc 

Downstream Products

• 848473-98-3 2-hydroxy-3-{5-[(3-oxopiperazin-1-yl)methyl]pyridin-2-yl}-1H-indole-6-carbonitrile hydrochloride 
• 1168152-02-0 (E)-1-acetyl-6-cyano-3-(ethoxy-phenyl-methylene)-indolin-2-one 

Relevant articles and documents

Discovery of Indolinone-Based Multikinase Inhibitors as Potential Therapeutics for Idiopathic Pulmonary Fibrosis

Idiopathic pulmonary fibrosis (IPF) is a serious and deadly disease for which treatment options are limited. The recent approval of antifibrosis agent nintedanib represents one of the first therapeutic approaches for the treatment of IPF. Here, we report novel indolinone-based multikinase inhibitors that target angiogenesis and fibrosis pathways and may serve as potential therapeutics for IPF. KBP-7018 is a novel, tyrosine kinase-selective inhibitor with potent effects on three fibrotic kinases (c-KIT, PDGFR, and RET). The pharmacokinetics (PK) properties of KBP-7018 were favorable in mice, rats, and dogs. In a bleomycin (BLM)-induced mouse pulmonary fibrosis model, 10, 30, and 100 mg/kg daily doses (q.d.) of KBP-7018 improved the 28-day survival rate in a dose-dependent manner. The improved efficacy of KBP-7018 compared to nintedanib provided a certain level of chemical validation for the involvement of PDGFR, c-KIT, and RET in IPF. Thus, KBP-7018 represents a novel multikinase inhibitor with differentiated activity, highly enhanced selectivity, and acceptable PK profiles that will enter phase I clinical trials.

Design, synthesis, and evaluation of indolinones as triple angiokinase inhibitors and the discovery of a highly specific 6-methoxycarbonyl-substituted indolinone (BIBF 1120)

Inhibition of tumor angiogenesis through blockade of the vascular endothelial growth factor (VEGF) signaling pathway is a newtreatment modality in oncology. Preclinical findings suggest that blockade of additional pro-angiogenic kinases, such as fibroblast and platelet-derived growth factor receptors (FGFR and PDGFR), may improve the efficacy of pharmacological cancer treatment. Indolinones substituted in position 6 were identified as selective inhibitors of VEGF-, PDGF-, and FGF-receptor kinases. In particular, 6-methoxycarbonyl-substituted indolinones showed a highly favorable selectivity profile. Optimization identified potent inhibitors of VEGF-related endothelial cell proliferation with additional efficacy on pericyctes and smooth muscle cells. In contrast, no direct inhibition of tumor cell proliferation was observed. Compounds 2 (BIBF 1000) and 3 (BIBF 1120) are orally available and display encouraging efficacy in in vivo tumor models while being well tolerated. The triple angiokinase inhibitor 3 is currently in phase III clinical trials for the treatment of nonsmall cell lung cancer.

Multicyclic bis-amide MMP inhibitors

The present invention relates generally to bis-amide group containing pharmaceutical agents, and in particular, to multicyclic bis-amide MMP-13 inhibitor compounds. More particularly, the present invention provides a new class of MMP-13 inhibiting compounds, containing a pyrimidinyl bis-amide group in combination with a heterocyclic moiety, that exhibit an increased potency and solubility in relation to currently known bis-amide group containing MMP-13 inhibitors.